A new synthesis of π-electron conjngated phosphonates and phosphonic bis(diethylamides) and their SHG activities

被引:67
作者
Ogawa, T
Usuki, N
Ono, N
机构
[1] Ehime Univ, Fac Sci, Dept Chem, Matsuyama, Ehime 790, Japan
[2] Kyushu Univ, Inst Fundamental Res Organ Chem, Fukuoka 81281, Japan
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 17期
关键词
D O I
10.1039/a709082j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of vinylic and arylic phosphonates and phosphonic bis(diethylamides) were prepared by copper promoted substitution of the corresponding bromides. These pi-electron conjugated phosphonates and phosphonic bis(diethylamides) were investigated to elucidate their optical and second harmonic generation (SHG) properties; it was found that diphenyl 2-(4-dimethylaminophenyl)ethenylphosphonate exhibited strong SHG activity, the efficiency being 13 times greater than that of urea.
引用
收藏
页码:2953 / 2958
页数:6
相关论文
共 51 条
[1]   CONVENIENT METHODS FOR THE PREPARATION OF PARA-DIALKYLAMINOPHENYLACETYLENES [J].
AKIYAMA, S ;
NAKATSUJI, S ;
YOSHIDA, K ;
NAKASHIMA, K ;
HAGIWARA, T ;
TSURUTA, H ;
YOSHIDA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (01) :361-362
[2]   CHEMISTRY OF HETEROARYLPHOSPHORUS COMPOUNDS .2. IMPORTANCE OF INDUCTIVE EFFECTS OF PRE-EQUILIBRIA IN ALKALINE-HYDROLYSIS OF HETEROARYLPHOSPHONIUM SALTS - PHOSPHORUS-31 NUCLEAR MAGNETIC-RESONANCE STUDIES [J].
ALLEN, DW ;
MELLOR, MTJ ;
HUTLEY, BG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1972, (01) :63-&
[3]   CHEMISTRY OF HETEROARYLPHOSPHORUS COMPOUNDS .7. HETEROARYLPHOSPHONATE, HETEROARYLMETHYLPHOSPHONATE, AND SUBSTITUTED ARYL-PHOSPHONATE ESTERS - ELECTRONIC EFFECTS OF SUBSTITUENTS AT PHOSPHORUS ON RATES OF ALKALINE-HYDROLYSIS, AND P-31 NUCLEAR MAGNETIC-RESONANCE AND PHOSPHORYL IR STRETCHING FREQUENCY STUDIES [J].
ALLEN, DW ;
HUTLEY, BG ;
MELLOR, MTJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1977, (06) :789-795
[4]  
ANTONOVA AB, 1987, ZH OBSHCH KHIM+, V57, P1030
[5]   ELECTROPHILIC SUBSTITUTION REACTIONS OF TRIPHENYLAMINE [J].
BAKER, TN ;
DOHERTY, WP ;
KELLEY, WS ;
NEWMEYER, W ;
ROGERS, JE ;
SPALDING, RE ;
WALTER, RI .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (11) :3714-&
[6]   THE MICHAELIS-ARBUZOV REARRANGEMENT [J].
BHATTACHARYA, AK ;
THYAGARAJAN, G .
CHEMICAL REVIEWS, 1981, 81 (04) :415-430
[7]   Stark spectroscopy of donor/acceptor substituted polyenes [J].
Bublitz, GU ;
Ortiz, R ;
Marder, SR ;
Boxer, SG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (14) :3365-3376
[8]   Stark spectroscopy of donor-acceptor polyenes: Correlation with nonlinear optical measurements [J].
Bublitz, GU ;
Ortiz, R ;
Runser, C ;
Fort, A ;
Barzoukas, M ;
Marder, SR ;
Boxer, SG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) :2311-2312
[9]   CRYSTAL-STRUCTURE AND MOLECULAR-ORBITAL CALCULATIONS OF TRANS-1-(2-CHLORO-4-DIMETHYLAMINOPHENYL)-2-NITROETHYLENE [J].
CAMERON, TS ;
COWLEY, DJ ;
THOMPSON, JE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (07) :774-777
[10]  
*CHEM SOC JAP, 1994, 68 NAT M CHEM SOC JA